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Synlett

Volumn , Issue 5, 2009, Pages 0787-0789

Azide-free synthesis of oseltamivir from L-methionine

(2) Oshitari, Tetsuta a,b Mandai, Tadakatsu a

a KURASHIKI UNIVERSITY OF SCIENCE AND THE ARTS (Japan)

b TEIKYO UNIVERSITY (Japan)

Author keywords

Anti influenza drugs; Hydroformylations; Intramolecular aldol condensation; Staudinger reaction; Tamiflu

Indexed keywords

EID: 62349105131 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1087940 Document Type: Article

Times cited : (38)

References (40)

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23
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27
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28
- 62349124329
- The desired cis-β-lactam 7a was easily purified by trituration in cold MeOH to remove byproducts such as minor stereoisomers (ca. 5, and N-(4-methoxyphenyl, 3-pentyloxy)acetamide. Compound 7a: a white solid; [α]D22 -119 (c 0.99 CHCl 3, mp 161.6-162.6°C. 1H NMR (500 MHz, CDCl 3, δ, 7.39 (br d, J, 8.9 Hz, 2 H, 6.87 (br d, J, 8.9 Hz, 2 H, 5.09 (br d, J, 10.1 Hz, 1 H, 4.78 (d, J, 5.5 Hz, 1 H, 4.56 (m, 1 H, 4.40 (dd, J, 5.5, 5.8 Hz, 1 H, 3.79 (s, 3 H, 3.61 (tt, J, 5.8, 5.8 Hz, 1 H, 2.55 (ddd, J, 4.6, 8.6, 13.1 Hz, 1 H, 2.38 (ddd, J, 7.9, 8.3, 13.1 Hz, 1 H, 1.93 (m, 1 H, 1.87 (s, 3 H, 1.80 (m, 1 H, 1.72 (m, 2 H, 1.62 (m, 2 H, 1.51-1.43 (two br s, 9 H, 1.94 (m, 6 H, 13C NMR 125 MHz, CDCl3, δ, 165.3, 156.6, 155.7, 130.6, 118.4, 114.6, 84.5, 81.1, 79.6, 57.3, 55.5, 48.7
- 5S: C, 61.77; H, 8.21; N, 6.00. Found: C, 61.87; H, 8.31; N, 6.16.

29
- 62349115112
- R (ent-7a) = 9.9 min.
- R (ent-7a) = 9.9 min.

30
- 0000280515
- A mixture of 7b (1.55 g, ca. 3.22 mmol, NaHCO3 (2.70 g, 32.2 mmol, α-pinene (10 mL, and decalins (10 mL) was placed into a 100 mL round-bottomed flask fitted with a reflux condenser. The reaction mixture was deoxygenated by alternate evacuation-argon flush cycles (five iterations) and heated with vigorous stirring at 150-155°C for 6 h under argon atmosphere. After being cooled to r.t, the reaction mixture was partitioned between H2O (30 mL) and EtOAc (30 mL, The organic layer separated was washed with brine (2 x 30 mL, dried (MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (hexane-EtOAc, 1:0 to 20:1 to 10:1 to 6:1) to give olefin 8a as a white solid (1.09 g, 81% from 7a, α]D26 -93.6 (c 1.03, CHCl3, mp 116.9-117.4°C. 1H NMR (500 MHz, CDCl3, δ, 7.35 (d, J, 8.8 Hz, 2 H, 6.87 d
- 3): δ = 165.2, 156.4, 133.8, 130.7, 118.6, 114.5, 106.3, 84.4, 81.0, 79.7, 57.5, 55.5, 52.3, 28.4, 26.5, 25.5, 9.6, 9.3. For thermal elimination of a methionine-derived sulfoxide, see: (a) Ohfune, Y.; Kurokawa, N. Tetrahedron Lett. 1984, 25, 1071.

31
- 0025016497
- For our previous protocol of thermal desulfinylation, see also: Mandai, T.; Matsumoto, S.; Kohama, M.; Kawada, M.; Tsuji, J.; Saito, S.; Moriwake, T. J. Org. Chem. 1990, 55, 5671.
- (b) For our previous protocol of thermal desulfinylation, see also: Mandai, T.; Matsumoto, S.; Kohama, M.; Kawada, M.; Tsuji, J.; Saito, S.; Moriwake, T. J. Org. Chem. 1990, 55, 5671.

32
- 62349094898
- Compound 8c: white solid; [α]D25 -14.4 (c 0.86 CHCl3, mp 111.6-111.8°C. 1H NMR (500 MHz, CDCl3, δ, 7.60-7.55 (br s, 4 H, 6.96 (d, J, 8.8 Hz, 2 H, 6.39 (d, J, 8.8 Hz, 2 H, 6.20 (ddd, J, 6.1, 10.0, 17.0 Hz, 1 H, 5.33-5.26 (m, 3 H, 5.03 (dd, J, 5.2, 10.3 Hz, 1 H, 4.89 (d, J, 5.2 Hz, 1 H, 3.65 (tt, J, 5.5, 5.5 Hz, 1 H, 3.45 (s, 3 H, 1.72 (m, 2 H, 1.61 (m, 2 H, 1.02 (t, J, 7.5 Hz, 3 H, 0.92 (t, J, 7.5 Hz, 3 H, 13C NMR 125 MHz, CDCl3, δ, 167.8, 166.0, 156.9, 134.2, 133.5, 131.7, 131.4, 128.1, 123.5, 122.8, 122.7, 119.0, 118.5, 114.5, 113.8, 83.3, 80.3, 57.3, 55.1, 53.0, 26.2, 25.3, 9.4, 9.2. Anal. Calcd for C26H28N2O5: C, 69.63, H, 6.29, N, 6.25. Found: C, 69.25; H, 6.10; N, 6.29
- 5: C, 69.63, H, 6.29, N, 6.25. Found: C, 69.25; H, 6.10; N, 6.29.

33
- 0019932198
- Kronenthal, D. R.; Han, C. Y.; Taylor, M. K. J. Org. Chem. 1982, 47, 2765.
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- Kronenthal, D.R.¹ Han, C.Y.² Taylor, M.K.³

34
- 84921186420
- Cuny, G. D.; Buchwald, S. L. J. Am. Chem. Soc. 1993, 115, 2066.
- (1993) J. Am. Chem. Soc , vol.115 , pp. 2066
- Cuny, G.D.¹ Buchwald, S.L.²

35
- 62349094904
- 6,6′, 3,3′-bis(1,1-dimethylethyl)-5,5′-dimethoxy[1, 1′-biphenyl]-2,2′-diyl]bis(oxy)}bis{dibenzo[d,f][1,3,2] dioxaphosphepine, a) Billig, E, Abatjoglou, A. G, Bryant, D. R. US 4668651, 1987
- 6,6′-{[3,3′-bis(1,1-dimethylethyl)-5,5′-dimethoxy[1, 1′-biphenyl]-2,2′-diyl]bis(oxy)}bis{dibenzo[d,f][1,3,2] dioxaphosphepine}: (a) Billig, E.; Abatjoglou, A. G.; Bryant, D. R. US 4668651, 1987.

36
- 62349101126
- US 4769498, for preparation of BIPHEPHOS, see Supporting Information of ref. 17
- (b) Billig, E.; Abatjoglou, A. G.; Bryant, D. R. US 4769498, 1988; for preparation of BIPHEPHOS, see Supporting Information of ref. 17.
- (1988)
- Billig, E.¹ Abatjoglou, A.G.² Bryant, D.R.³

37
- 0025073031
- Fukuyama, T.; Lin, S.-C.; Li, L. J. Am.Chem. Soc. 1990, 112, 7050.
- (1990) J. Am.Chem. Soc , vol.112 , pp. 7050
- Fukuyama, T.¹ Lin, S.-C.² Li, L.³

38
- 0000679083
- (a) Corey, E. J.; Danheiser, R. L.; Chandrasekaran, S.; Siret, P.; Keck, G. E.; Gras, J.-L. J. Am. Chem. Soc. 1978, 100, 8031.
- (1978) J. Am. Chem. Soc , vol.100 , pp. 8031
- Corey, E.J.¹ Danheiser, R.L.² Chandrasekaran, S.³ Siret, P.⁴ Keck, G.E.⁵ Gras, J.-L.⁶

39
- 33344454722
- (b) Snyder, S. A.; Corey, E. J. Tetrahedron Lett. 2006, 47, 2083.
- (2006) Tetrahedron Lett , vol.47 , pp. 2083
- Snyder, S.A.¹ Corey, E.J.²

40
- 62349100494
- Compound 12: off-white solid; [α]D23.4 -44.0 (c 1.05, CHCl3, mp 198-199.1°C. 1H NMR (500 MHz, CDCl3, data of a mixture of rotamers, δ, 9.56 (s, 0.15 H, 9.54 (s, 0.85 H, 7.86-7.72 (m, 4 H, 6.68 (s, 0.15 H, 6.67 (s, 0.85 H, 5.58 (d, J, 7.6 Hz, 0.85 H, 5.26 (d, J, 7.6 Hz, 0.15 H, 4.95-4.87 (m, 0.85 H, 4.75-4.71 (m, 0.85 H, 4.50-4.32 (m, 1.15 H, 4.15-4.10 (m, 0.15 H, 3.46-3.33 (m, 1 H, 3.10-2.97 (m, 1 H, 2.76-2.65 (m, 1 H, 2.05 (s, 0.45 H, 1.78 (s, 2.55 H, 1.60-1.50 (m, 4 H, 1.00-0.85 (m, 6 H, 13C NMR 125 MHz, CDCl3, data of a mixture of rotamers, δ, 192.2, 170.3, 168.1, 147.5, 138.8, 134.2, 131.6, 123.4, 82.4, 74.6, 54.3, 47.8, 26.3, 25.7, 25.5, 23.3, 9.6, 9.3. Anal. Calcd for C 22H26N2O5: C, 66.32, H, 6.58, N, 7.03. Found: C, 66.06; H, 6.72; N, 6.98
- 5: C, 66.32, H, 6.58, N, 7.03. Found: C, 66.06; H, 6.72; N, 6.98.

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